Activated anionic ring-opening polymerization for the synthesis of reversibly cross-linkable poly(propylene oxide) based on furan/maleimide chemistry

The synthesis of cross-linkable random copolyethers of propylene oxide (PO) and furfuryl glycidyl ether (FGE) is first discussed. The anionic ring-opening polymerization and monomer activation methodology, based on the combination of tetraoctylammonium bromide and triisobutylaluminum, is used to per...

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Bibliographic Details
Published in:Polymer chemistry 2016-01, Vol.7 (8), p.1612-1622
Main Authors: Roos, Kévin, Dolci, Elena, Carlotti, Stéphane, Caillol, Sylvain
Format: Article
Language:English
Subjects:
Chemical Sciences
Copolymers
Crosslinking
Ethers
Furans
Networks
Polymerization
Polymers
Synthesis
Three dimensional
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Summary:The synthesis of cross-linkable random copolyethers of propylene oxide (PO) and furfuryl glycidyl ether (FGE) is first discussed. The anionic ring-opening polymerization and monomer activation methodology, based on the combination of tetraoctylammonium bromide and triisobutylaluminum, is used to perform the controlled synthesis of poly(propylene oxide- co -furfuryl glycidyl ether) copolymers with various compositions 95/5, 90/10, 75/25, 50/50, and 25/75 (PO/FGE mol%) and keeping the furfuryl moieties active. Copolymers with molar masses around 10 000 g mol −1 were obtained in short times. Subsequently, the furfuryl moieties were reacted with aromatic and aliphatic maleimide-based cross-linkers to perform Diels-Alder (DA) "click" reactions. Three-dimensional networks were obtained and their swelling ratio and insoluble fraction were determined. Glass transition temperature and retro-Diels-Alder (rDA) transition in the network were determined by differential scanning calorimetry analyses. Gel properties vary with the furan group amount in the initial copolymer and the cross-linker structure. The network disassembly at 110 °C was monitored by 1 H NMR and quantitatively recorded by the re-appearance of the copolymer signals due to the rDA reaction. The solubility study showed that the gel was able to reform at 20 °C leading to reversible cross-linked polyethers. Controlled anionic copolymerization of propylene oxide and furfuryl glycidyl ether was developed for the synthesis of reversibly cross-linkable polyethers.
ISSN:1759-9954
1759-9962
DOI:10.1039/c5py01778e